Acetyl chloride → N-Acetyl-L-serine methyl ester

HRID 235710

Reaktionsgleichung

Reaktionsgleichung von HRID 235710
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18]>C(Cl)(Cl)Cl>[C:17]([NH:6][C@H:5]([C:4]([O:3][CH3:2])=[O:9])[CH2:7][OH:8])(=[O:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Produkt 1

HCID 7010549N-Acetyl-L-serine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a suspension of about 46.57 g of L-serine methyl ester hydrochloride in about 3 liters of chloroform was added about 84 ml of triethylamine. This mixture was stirred until solution was complete, then about 21 ml of acetyl chloride was added dropwise. The mixture was then stirred under argon for about 2 days and the chloroform removed under reduced pressure. The residue was suspended in ethanol, filtered through a sintered glass funnel and the ethanol removed, giving about 49 g of the desired title compound [α]D26 =+36°±1° (CHCl3, 1.039%).

Aufarbeitung

  1. stirringThe mixture was then stirred under argon for about 2 days
  2. customthe chloroform removed under reduced pressure
  3. filtrationfiltered through a sintered glass funnel
  4. customthe ethanol removed

Quellen und Nachweise

ORD-Eintrag
ord-a2cbcbd39a6b4bd0989d6e6ebf5761a8
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04640913

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